“Hindsight is 20/20.”

“If I only knew then what I know now.”

“Monday morning quarterbacking.”

Back in 2007, things were going pretty well for me. I had a great job, owned a nice house, and lived a pretty solid life. It was an interesting time. The first iPhone had just come out. A new president was about to take office…

And the market crash of 2008 was looming around the corner.

I wish I could have known it was coming. We have lots of expressions for reviewing the past with our knowledge of the present.

But there’s another one: “Those who refuse to learn from history are doomed to repeat it” that’s more useful.

Here’s a list of 5 things that I wish I knew when I started Rain City Capital back in 2007.

Always be who you are – Sometimes we get caught up in who we’d like to be rather than understanding who we are. The most successful people I meet are those that know exactly who they are. They work to their strengths rather than try to be someone they’re not. I’m completely unorganized and I’ve learned to own it. I don’t try to act organized and warn people that organization isn’t my strong suit. Another example—I’m not a great sales person. Yet, I am trustworthy and great at solving problems creatively. Rather than read every sales book ever to improve, I’ve put myself in a position that plays to my strengths.

Pick your partners wisely! – I’ve had several partnerships, both good and bad, over the last 14+ years of investing. A good partner is invaluable, but if you have red flags going into a partnership, walk away. Usually, the money won’t be as great as you anticipated and the accompanying stress isn’t worth the payoff. The foundation of a good partnership includes:

  • Mutual Respect: The most important element—and it has to go both ways.
  • Mutual Benefit: A real partnership is a win/win for everyone involved. And the win doesn’t have to be monetary.
  • Mutual Understanding: Who is doing what—and why? Is that their strength or are they going to flop? Knowing the answers to these questions is the key to a good partnership.

Don’t put all your eggs in one basket. – This adage is well known, yet practiced so little. About one third of Americans have no savings at all, and another third have less than $1K in the bank. As investors, we’re encouraged to be bold. To take risks. We have a hard time spreading our money around. We believe we can get a better return than some random broker… and oftentimes we’re even right. However, your broker won’t lose all your capital like you might on that big deal you knew would make you rich.

In 2008, as some of you know from our company video, I nearly lost everything. I thought I was smarter than everyone around me. I learned from my mistakes the hard way and it shapes all my financial decisions today. Take some off the table on every transaction and you’ll thank me in 30 years!

Markets change! – In 2005 and 2006, I was doing short sales before anyone else knew what they were. Then from 2009 to 2011, everyone was short-selling their home. Now, short sales are rare because the market is so strong. If you find a niche, don’t think it will last forever. It won’t. Someone will find a way to do it better and you’re out of business. Do your homework. Keep up with market trends. Plan for the next niche and build your business… don’t just coast on your success and stand idly by.

Beware the slippery slope of bulls&%t – In this crazy real estate business, you’ll meet SO MANY great talkers that try to sell you on “hot” ideas. Watch out! Those dreams of $100 bills raining down from the sky while hanging on a yacht with Mark Cuban might leave you on the corner begging for change. Greater talkers are exactly that… great talkers. They might be able to back it up, but I’ve met too many who wasted my time and money. It’s far more important to find your niche and stay the course. That’s how you become successful—there are no quick and easy ways to make it happen.